CHEBI:6912 - α-methyl-L-tyrosine

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ChEBI Name α-methyl-L-tyrosine
ChEBI ID CHEBI:6912
ChEBI ASCII Name alpha-methyl-L-tyrosine
Definition An L-tyrosine derivative that consists of L-tyrosine bearing an additional methyl substituent at position 2. An inhibitor of the enzyme tyrosine 3-monooxygenase, and consequently of the synthesis of catecholamines. It is used to control the symptoms of excessive sympathetic stimulation in patients with pheochromocytoma.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C10H13NO3
Net Charge 0
Average Mass 195.21510
Monoisotopic Mass 195.08954
InChI InChI=1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)/t10-/m0/s1
InChIKey NHTGHBARYWONDQ-JTQLQIEISA-N
SMILES C[C@](N)(Cc1ccc(O)cc1)C(O)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): EC 1.14.16.2 (tyrosine 3-monooxygenase) inhibitor
An EC 1.14.16.* (oxidoreductase acting on paired donors, reduced pteridine as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosine 3-monooxygenase (EC 1.14.16.2).
Application(s): antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
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ChEBI Ontology
Outgoing α-methyl-L-tyrosine (CHEBI:6912) has role antihypertensive agent (CHEBI:35674)
α-methyl-L-tyrosine (CHEBI:6912) has role EC 1.14.16.2 (tyrosine 3-monooxygenase) inhibitor (CHEBI:63932)
α-methyl-L-tyrosine (CHEBI:6912) is a L-tyrosine derivative (CHEBI:27177)
α-methyl-L-tyrosine (CHEBI:6912) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
IUPAC Name
α-methyl-L-tyrosine
INNs Sources
metirosina ChemIDplus
metirosine KEGG DRUG
metirosinum ChemIDplus
Synonyms Sources
(-)-alpha-Methyl-L-tyrosine ChemIDplus
(S)-alpha-Methyltyrosine ChemIDplus
α-methyl-L-p-tyrosine ChEBI
α-methyl-p-tyrosine ChEBI
α-methyl-para-tyrosine ChEBI
alpha-Methyltyrosine ChemIDplus
L-alpha-Methyltyrosine ChemIDplus
Methyltyrosine DrugBank
Metyrosine KEGG COMPOUND
Manual Xrefs Databases
1792 DrugCentral
C07921 KEGG COMPOUND
D00762 KEGG DRUG
DB00765 DrugBank
Metirosine Wikipedia
US2011104765 Patent
View more database links
Registry Numbers Types Sources
2368400 Reaxys Registry Number Reaxys
672-87-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
28716505 PubMed citation Europe PMC
29353821 PubMed citation Europe PMC
29438107 PubMed citation Europe PMC
29668781 PubMed citation Europe PMC
Last Modified
22 June 2018